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University of Groningen Enzymatic Synthesis and Polymerization of Saccharide-Vinyl Monomers in Aqueous Systems Adharis, Azis

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Enzymatic Synthesis and Polymerization of Saccharide-Vinyl Monomers in Aqueous Systems

Adharis, Azis

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from

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Publication date:

2019

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Adharis, A. (2019). Enzymatic Synthesis and Polymerization of Saccharide-Vinyl Monomers in Aqueous

Systems. University of Groningen.

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Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum.

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Enzymatic Synthesis and Polymerization

of Saccharide-Vinyl Monomers

in Aqueous Systems

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University of Groningen June 2019

Zernike Institute PhD thesis series 2019-17 ISSN: 1570-1530

ISBN: 978-94-034-1750-9 (printed version) ISBN: 978-94-034-1749-3 (electronic version)

The research presented in this thesis was performed in the research group of Macromo-lecular Chemistry and New Polymeric Materials of the Zernike Institute for Advanced Materials at the University of Groningen, The Netherlands. Azis Adharis received a PhD scholarship from Lembaga Pengelola Dana Pendidikan (Indonesian Endowment Fund for Education), Ministry of Finance, Republic of Indonesia.

Cover design: Dina Maniar, dina.maniar09@gmail.com Layout design: Jules Verkade, www.persoonlijkproefschrift.nl Printing: Ipskamp printing, www.proefschriften.net © 2019, Azis Adharis

All rights reserved. No part of this thesis may be reproduced, stored, or transmitted in any form or by any means without the prior permission of the copyright holder, or when ÖťťķĢóÖðķā̇ŋĕŶĞāťŽðķĢŭĞāũŭŋĕŶĞāŭóĢāłŶĢƩóťÖťāũŭ̍

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Enzymatic Synthesis and Polymerization

of Saccharide-Vinyl Monomers

in Aqueous Systems

PhD thesis

to obtain the degree of PhD at the University of Groningen

on the authority of the ˜āóŶŋũmÖėłĢƩóŽŭťũŋĕ̍1̍œŶāũĴāł

and in accordance with the decision by the College of Deans. This thesis will be defended in public on

Friday 28 June 2019 at 9.00 hours

by

Azis Adharis born on 3 August 1987

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Assessment Committee

Prof. K. Barta

Prof. A. Gandini Prof. R. Liska

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Contents

Chapter 1: General Introduction

1.1 Carbohydrates 10

1.2 Enzymes as biocatalysts in synthetic organic chemistry 14 1.3 Enzymatic synthesis of saccharide-vinyl (macro)monomers 17

1.4 Glycopolymers 29

1.5 Aim and outline of the thesis 33

1.6 References 35

Chapter 2: Synthesis of (Meth)Acrylamide-Based Glycomonomers Using Renewable Resources and Their Polymerization in Aqueous Systems

2.1 Introduction 42

2.2 Experimental 43

2.3 Results and discussion 47

2.4 Conclusions 55

2.5 References 57

Chapter 3: Environmentally Friendly Pathways Towards the Synthesis of Vinyl-Based Oligocelluloses

3.1 Introduction 62

3.2 Experimental 63

3.3 Results and discussion 67

3.4 Conclusions 76

3.5 References 77

Chapter 4: Green Synthesis of Glycopolymers Using an Enzymatic Approach

4.1 Introduction 82

4.2 Experimental 83

4.3 Results and discussion 85

4.4 Conclusions 92

4.5 References 93

Chapter 5: Synthesis and Self-Assembly of Double-Hydrophilic and Amphiphilic Block Glycopolymers

5.1 Introduction 98

5.2 Experimental 99

5.3 Results and discussion 104

5.4 Conclusions 112

5.5 References 114

Summary 118

Samenvatting 122

Acknowledgments 126

About the Author 130

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